WO2025081339A1

WO2025081339A1 - Cosmetic product comprising 4-t-butylcyclohexanol, monoglyceryl ester and an oil

Info

Publication number: WO2025081339A1
Application number: PCT/CN2023/124942
Authority: WO
Inventors: Luan LUAN; Hanjun CHEN
Original assignee: Nivea Shanghai Co Ltd; Beiersdorf AG
Current assignee: Nivea Shanghai Co Ltd; Beiersdorf AG
Priority date: 2023-10-17
Filing date: 2023-10-17
Publication date: 2025-04-24
Anticipated expiration: 2026-04-17
Also published as: WO2025083018A1

Abstract

It relates to a cosmetic composition comprising 4-t-butylcyclohexanol, at least one further branched alcohol having 14 to 26 carbon atoms, and one or more monoglyceryl ester, No or less crystals are formed by the composition.

Description

Cosmetic product comprising 4-t-butylcyclohexanol, monoglyceryl ester and an oil

Technical field

The present invention belongs to the cosmetic field and relates to a cosmetic composition comprising 4-t-butylcyclohexanol, monoglyceryl ester and an oil which is an alcohol.

Background art

Cosmetic products generally not only serve to look beautiful and attractive, but their effects make a decisive contribution to increased self-esteem and people's wellbeing. Accordingly, a wide variety of cosmetic products are used for the daily cleaning and care of human skin.

A well-known group of cosmetic products are body lotions and cosmetic face care products. The formulations are usually formulated as oil in water emulsion or are in gel form. In the past the formulations contained silicone oils and polymers polymerized in a homo or copolymerization with acrylic acid and/or methacrylic acid. Those compounds allowed for a pleased sensory, so that the lotion can be easy spread over the skin providing a fresh non sticky feeling. The formulations do absorb easily. Thereby, the named polymers are often used to thicken the formulations to the right viscosity such that the formulations have a rich body and do not easily run off the skin. Further the polymers provide the benefit that the formulas are stable, and no phase separation or crystallization of ingredients occurs.

However, it is desirable for various reason to provide formulations free from both silicones and polymers polymerized in a homo or copolymerization with acrylic acid and/methacrylic acid. Although this approach sounds simple various problems may occur in the formulation process.

Further, it is often the case that well-known cosmetic products do comprise Polyethyleneglycol derivatives as emulsifier, such as PEG-40 hydrogenated castor oil. However, consumers prefer to use formulation not containing Polyethyleneglycol derivatives for various reasons. Thus, it is desirable to not contain those ingredients in cosmetic formulations.

Typically, cosmetic care formulations comprise active ingredients to achieve a skin benefit. One ingredient occasionally used in cosmetic formulations is 4-t-butylcyclohexanone. The component is traded under the trade name1609 in form of a clear synthetic liquid solution used for fast skin relief. It significantly alleviates stinging and burning by reducing stinging up to 78%after 3 minutes and burning up to 80%after 3 minutes. It is proven to smoothen scalp sensitivities of burning and stinging during chemical color treatment. Besides 4-t-butylcyclohexanone1609 contains pentylene glycol.

One example of typical problem which may arise in proving desirable formulation with 4-t-butylcyclohexanone is that crystals may be formed in the composition if stored at 6℃ for 3 days. This condition typically appears upon storage and transport of the formulations. This effect most often occurs in formulations having a low viscosity ranging from 300 to 1000 mPa·s.

Thus, it is the objective of the present invention to address this shortfall.

Cosmetic formulations with 4-t-butylcyclohexanol are disclosed in WO2009/087242 A2. However, the document could not direct the person skilled in art in the direction of the present invention.

Summary of the invention

The present invention is a cosmetic composition comprising an aqueous phase and an oil phase characterized in that the composition comprises

a) 4-t-butylcyclohexanol,

b) At least one further branched alcohol having 14 to 26 carbon atoms,

c) One or more monoglyceryl ester,

whereby the composition is free from polymers polymerized from a mixture comprising or consisting of acrylic acid and/or methacrylic acid.

It was surprisingly further noted that no or less crystals are formed by the composition according to the present invention.

Definitions

All the weight percentages (%by weight) given below relate, unless otherwise stated, to the total weight of the cosmetic composition.

If ratios of certain components are disclosed in the following description, these ratios refer, unless otherwise stated, to weight ratios of the components.

Unless otherwise stated, all tests and measurements were performed under “normal conditions” . The term "normal conditions" refers to 25℃, 1013 hPa and a relative humidity of 50%.

In the following description the terms “according to the invention” , “preferred according to the invention” and so on are always directed to the use according to the invention, to the composition and to the method according to the invention.

For the purposes of the present disclosure, the term "free from" means that the proportion of the respective substance is less than 0.01%by weight. This ensures that entrainments or impurities with these substances are not included as "free from" according to the invention.

The term “skin” refers solely to the human skin.

If viscosity values are given in this disclosure, then all values relate to a measurement at 25℃. in a 150 ml wide-mouth bottle (VWR No.: 807-001) using Rheomat R 123 from the company proRheo. The Rheomat R 123 from proRheo GmbH is a rotational viscometer, i. H. a measuring body rotates in the substance to be measured. The force required to rotate the measuring body in the sample at a specified speed is measured. The viscosity is calculated from this torque, the speed of the measuring body and the geometric dimensions of the measuring system used. Measuring body No. 1 (Article No. 200 0191) , suitable for a viscosity range of up to 10,000 [mPa s] , speed range 62.5 min^-1, is used as the measuring body.

Emulsifiers are understood to be all substances which are listed in the International Cosmetic Ingredient Dictionary and Handbook, Thirteenth Edition 2010, (ISBN 1-882621-47-6) under the name "emulsifying agent" . Surfactants are understood to be all substances which are listed in the International Cosmetic Ingredient Dictionary and Handbook, Thirteenth Edition 2010, (ISBN 1-882621-47-6) under the name "surfactant" .

The term “at least one” refers to one or more.

Detailed description

The composition according to the present invention comprises 4-t-butylcyclohexanol. It is preferred if the total quantity of 4-t-butylcyclohexanol is in the range from 0.05 to 5%by weight, more preferably from 0.1 to 1.0%by weight and most preferably from 0.15 to 0.3%by weight, calculated to the total weight of the composition.

4-t-butylcyclohexanol can be used in cis or in trans modification. According to the invention it is preferred if the composition comprises trans-4-t-butylcyclohexanol. It is particular preferred if the total quantity of trans-4-t-butylcyclohexanol is in the range from 0.05 to 5%by weight, more preferably from 0.1 to 1.0%by weight and most preferably from 0.15 to 0.3%by weight, calculated to the total weight of the composition.

For the case that both cis-and trans-4-t-butylcyclohexanol are contained it is preferred if the ratio by weight between cis-and trans-4-t-butylcyclohexanol is in the range from 100: 1 to 1: 100, more preferably 10: 1 to 1: 99 and most preferred 1: 1 to 1: 98.

The composition according to the present invention comprises at least one further branched alcohol having 14 to 26 carbon atoms. It is preferred if the at least one further branched alcohol is selected from alcohols having 16 to 24 carbon atoms, more preferably 18 to 22 carbon atoms and most preferably 20 carbon atoms.

In one embodiment of the invention, it is preferred if the total quantity of the at least one further branched alcohol having 14 to 26 carbon atoms is in the range from 0.1 to 5.0%by weight, more preferably from 0.2 to 2.0%by weight and most preferably 0.3 to 1.0%by weight, calculated to the total weight of the composition.

In one embodiment of the invention, it is preferred if the total quantity of the at least one further branched alcohol having 16 to 24 carbon atoms is in the range from 0.1 to 5.0%by weight, more preferably from 0.2 to 2.0%by weight and most preferably 0.3 to 1.0%by weight, calculated to the total weight of the composition.

In one embodiment of the invention, it is preferred if the total quantity of the at least one further branched alcohol having 18 to 22 carbon atoms is in the range from 0.1 to 5.0%by weight, more preferably from 0.2 to 2.0%by weight and most preferably 0.3 to 1.0%by weight, calculated to the total weight of the composition.

In one embodiment of the invention, it is preferred if the total quantity of the at least one further branched alcohol having 20 carbon atoms is in the range from 0.1 to 5.0%by weight, more preferably from 0.2 to 2.0%by weight and most preferably 0.3 to 1.0%by weight, calculated to the total weight of the composition.

It is preferred if hexyldecanol and/or octyldodecanol are contained as alcohols b) . Most preferred is octyldodecanol. It is preferred if hexyldecanol and/or octyldodecanol are contained in a total quantity in the range from 0.1 to 5.0%by weight, more preferably from 0.2 to 2.0%by weight and most preferably 0.3 to 1.0%by weight, calculated to the total weight of the composition.

The compositions according to the invention comprise at least one monoglyceryl ester. Monoglyceryl esters are understood as an ester formed from glycerol and at least one mono-or polyvalent fatty acid.

According to the invention, it is preferred if the total quantity of the monoglyceryl ester is in the range from 0.1 to 2.0%by weight, more preferably 0.3 to 1.5%by weight and most preferably 0.5 to 1.0%by weight, calculated to the total weight of the composition.

In one embodiment the one or more monoglyceryl esters are selected from glyceryl diisostearate, glyceryl stearate, glyceryl caprylate, glyceryl isostearate, glyceryl oleate and/or glyceryl behenate. It is preferred if the total quantity of glyceryl diisostearate, glyceryl stearate, glyceryl caprylate, glyceryl isostearate, glyceryl oleate and/or glyceryl behenate is in the range from 0.1 to 2.0%by weight, more preferably 0.3 to 1.5%by weight and most preferably 0.5 to 1.0%by weight, calculated to the total weight of the composition.

In one embodiment the one or more monoglyceryl esters are selected from esters made of a glycerin and one or more monovalent fatty acid comprising 16 to 20 carbon atoms. Preferred monoglyceryl ester is selected from glyceryl stearate, glyceryl stearate SE and/or glyceryl caprylate. It is preferred if the total quantity of glyceryl stearate, glyceryl stearate SE and/or glyceryl caprylate is in the range from 0.1 to 2.0%by weight, more preferably 0.3 to 1.5%by weight and most preferably 0.5 to 1.0%by weight, calculated to the total weight of the composition.

Further, it is preferred if the composition comprises sodium stearoyl glutamate. For the case that sodium stearoyl glutamate is contained, it is preferred if the total quantity of sodium stearoyl glutamate is in the range from 0.01 to 0.5%by weight, calculated to the total weight of the composition.

Further it is preferred if the total quantity of the oil phase in the cosmetic composition is in the range from 0.1 to 5.0%by weight, more preferably 0.2 to 2.5%by weight and most preferably from 0.3 to 2.0%by weight, calculated to the total weight of the composition. By definition, the total amount of emulsifier and surfactants do not count to the amount of the oil phase.

Preferred embodiments of the invention are further characterized in that at least one polysaccharide is contained a structuring agent for the composition. According to the invention it is preferred if the polysaccharide is a gum.

Preferred gums, which can be used according to the invention are selected from the group of xanthan gum, gellan gum, sclerotium gum and dehydroxanthan gum.

It is advantageous if the composition comprises 0.1 to 1.5%by weight, more preferably 0.15 to 1.0 %by weight and most preferably 0.3 to 0.8%by weight of at least one polymer selected from the group of xanthan gum, gellan gum, sclerotium gum and dehydroxanthan gum, calculated to the total weight of the composition. It is particular preferred if xanthan gum is contained and the total quantity of xanthan gum is in the range from 0.1 to 1.5%by weight, more preferably 0.15 to 1.0 %by weight and most preferably 0.3 to 0.8%by weight, calculated to the total weight of the composition.

It is particular preferred if at least xanthan gum is contained. It is particular preferred if xanthan gum is contained in a total quantity ranging from 0.1 to 1.5%by weight, more preferably 0.15 to 1.0 %by weight and most preferably 0.3 to 0.8%by weight calculated to the total weight of the composition.

According to the invention it is preferred if the composition is characterized in that it is an emulsion.

Further preferred compositions of the invention comprise hydroxypropyl starch phosphate. For the case that hydroxypropyl starch phosphate is contained, it is preferred if the total quantity of hydroxypropyl starch phosphate is in the range from 0.01 to 2.5%by weight, more preferably 0.4 to 2.4%by weight and most preferably 0.5 to 1.9%by weight calculated to the total weight of the composition.

Further it is preferred if the composition according to the invention comprises further short chain polyols comprising 2 to 8 carbon atoms. Preferred polyols of that type are butylene glycol, glycerol, propylene glycol, pentylene glycol, butylene glycol, 1, 2 hexanediol, 1, 2 heptanediol, 1, 2 propanediol, methylpropanediol and caprylyl glycol.

It is preferred if those preferred polyols are contained in quantities ranging from 0.1 to 15%by weight, more preferably 1 to 12%by weight and most preferably from 1.5 to 8%by weight, calculated to the total weight of the composition.

It is particular preferred if pentylene glycol is contained. For the case that pentylene glycol is contained it is preferred if the total quantity of pentylene glycol is in the range from 0.1 to 4.0%by weight, more preferably from 0.3 to 3.0%by weight and most preferably from 0.6 to 2.5%by weight, calculated to the total weight of the composition.

It is also particular preferred if glycerol is contained. For the case that glycerol is contained it is preferred if the total quantity of glycerol is in the range from 0.1 to 13.0%by weight, more preferably from 2.5 to 12.0%by weight and most preferably from 3.0 to 6.5%by weight, calculated to the total weight of the composition.

For the case that caprylyl glycol is contained, it is preferred if the total quantity of caprylyl glycol is in the range from 0.1 to 5%by weight, more preferably 0.2 to 2%by weight and most preferably from 0.3 to 1.5%by weight, calculated to the total weight of the composition.

Further it is preferred if the composition comprises phenoxyethanol, hydroxacetophenone and/or ethylhexylglycerin.

For the case that phenoxyethanol is contained it is preferred if the total quantity of phenoxyethanol is in the range from 0.1 to 0.8%by weight, calculated to the total weight of the composition.

For the case that ethylhexylglycerin is contained it is preferred if the total quantity of ethylhexylglycerin is in the range from 0.1 to 1.2%by weight, calculated to the total weight of the composition.

For the case that hydroxacetophenone is contained it is preferred if the total quantity of hydroxacetophenone is in the range from 0.1 to 0.5%by weight, calculated to the total weight of the composition.

Further it is preferred if water is contained in the composition in a total quantity ranging from 75.0%by weight to 95%by weight, e.g., 80%by weight, 85%by weight, or 90%by weight, calculated to the total weight of the composition.

According to the invention it is preferred if the composition has a viscosity ranging from 300 to 1000 mPa·s.

It is also advantageous according to the invention if further active ingredients are contained. These are advantageously selected from the group containing sodium hyaluronate, 1-methylhydantoin-2-imide, creatine, folic acid, panthenol, pantolactone, vitamin C, magnolia, calcium pantothenate, ectoin and sodium ascorbyl phosphate. The active ingredients mentioned in the group are advantageously used in total proportions of up to 10%by weight, preferably less than 1%by weight, based on the total weight of the composition.

The compositions according to the invention may further comprise ingredients commonly used in the compositions of this type.

Examples

The following examples should illustrate the compositions of this invention, without intending to limit the invention to these examples. The numerical values in the examples are percentages by weight, based on the total weight of the preparations.

Examples 1 is a composition according to the invention. Ex. 2 is a reference example not in scope of the invention.

The analysis for crystals was made in the following manner: After production of the examples, the examples were stored at 6℃ for a period of 3 days. Then the formulations were optically analyzed using a Nikon Eclipse Ci POL microscope 10x magnification to observe and identify crystals. If present the crystals had a needle shape.

Further examples Ex. 3-Ex. 8 according to the invention are disclosed in the following table:

Claims

Cosmetic composition comprising an aqueous phase and an oil phase characterized in that the composition comprises

a) 4-t-butylcyclohexanol,

b) At least one further branched alcohol having 14 to 26 carbon atoms, and

c) One or more monoglyceryl ester,

whereby the composition is free from polymers polymerized from a mixture comprising or consisting of acrylic acid and/or methacrylic acid.
Composition according to claim 1 characterized in that the total quantity of 4-t-butylcyclohexanol is in the range from 0.05 to 5%by weight, preferably from 0.1 to 1.0%by weight and more preferably from 0.15 to 0.3%by weight, calculated to the total weight of the composition.
Composition according to any of the proceeding claims characterized in that the composition comprises trans-4-t-butylcyclohexanol.
Composition according to any of the proceeding claims characterized in that both cis-and trans-4-t-butylcyclohexanol are contained.
Composition according to claim 4 characterized in that the ratio by weight between cis-and trans-4-t-butylcyclohexanol is in the range from 100: 1 to 1: 100, more preferably 10: 1 to 1: 99 and most preferably 1: 1 to 1: 98.
Composition according to any of the proceeding claims characterized in that the total quantity of the at least one further branched alcohol having 14 to 26 carbon atoms is in the range from 0.1 to 5.0%by weight, preferably from 0.2 to 2.0%by weight and more preferably 0.3 to 1.0%by weight, calculated to the total weight of the composition.
Composition according to any of the proceeding claim characterized in that the at least one further branched alcohol b) is selected from alcohols having 16 to 24 carbon atoms, and it is preferred if the total quantity of the at least one further branched alcohol having 16 to 24 carbon atoms is in the range from 0.1 to 5.0%by weight, more preferably from 0.2 to 2.0%by weight and most preferably 0.3 to 1.0%by weight, calculated to the total weight of the composition.
Composition according to any of the proceeding claim characterized in that the at least one further branched alcohol b) is selected from alcohols having 18 to 22 carbon atoms, and it is preferred if the total quantity of the at least one further branched alcohol having 18 to 22 carbon atoms is in the range from 0.1 to 5.0%by weight, more preferably from 0.2 to 2.0%by weight and most preferably 0.3 to 1.0%by weight, calculated to the total weight of the composition.
Composition according to any of the proceeding claim characterized in that the at least one further branched alcohol b) is selected from alcohols having 20 carbon atoms, and it is preferred if the total quantity of the at least one further branched alcohol having 20 carbon atoms is in the range from 0.1 to 5.0%by weight, more preferably from 0.2 to 2.0%by weight and most preferably 0.3 to 1.0%by weight, calculated to the total weight of the composition.
Composition according to any of the claims 1 to 5 characterized in that hexyldecanol and/or octyldodecanol are contained as alcohols b) .
Composition according to claim 10 characterized in that hexyldecanol and/or octyldodecanol are contained in a total quantity in the range from 0.1 to 5.0%by weight, preferably from 0.2 to 2.0%by weight and more preferably 0.3 to 1.0%by weight, calculated to the total weight of the composition.
Composition according to any of the proceeding claims characterized in that the one or more monoglyceryl esters are selected from glyceryl diisostearate, glyceryl stearate, glyceryl caprylate, glyceryl isostearate, glyceryl oleate and/or glyceryl behenate.
Composition according to claim 1 to 11 characterized in that the monoglyceryl ester are selected from glyceryl stearate, glyceryl stearate SE and/or glyceryl caprylate.
Composition according to any of the proceeding claims characterized in that the total quantity of the monoglyceryl ester is in the range from 0.1 to 2.0%by weight, preferably 0.3 to 1.5%by weight and more preferably 0.5 to 1.0%by weight, calculated to the total weight of the composition.
Composition according to any of the proceeding claims characterized in that the composition comprises sodium stearoyl glutamate, and it is preferred if the total quantity of sodium stearoyl glutamate is in the range from 0.01 to 0.5%by weight, calculated to the total weight of the composition.
Composition according to any of the proceeding claims characterized in that at least one polysaccharide gum selected from xanthan gum, gellan gum, sclerotium gum and dehydroxanthan gum is contained, and it is preferred if the total quantity of those gums is in the range from comprises 0.1 to 1.5%by weight, more preferably 0.15 to 1.0 %by weight and most preferably 0.3 to 0.8%by weight, calculated to the total weight of the composition.